# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1474749'
_audit_update_record             
;
2016-09-23 deposited with the CCDC.
2016-10-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H38 Cu3 N4 O16'
_chemical_melting_point          ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            Blue
_chemical_formula_weight         853.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1872(6)
_cell_length_b                   16.9482(13)
_cell_length_c                   11.7093(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.284(4)
_cell_angle_gamma                90
_cell_volume                     1593.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      27.28
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.778
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             874
_exptl_absorpt_coefficient_mu    2.066
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.5856
_exptl_absorpt_correction_T_max  0.7334
_exptl_absorpt_process_details   Sadabs

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEX'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17858
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2941
_reflns_number_gt                2404
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND 2.1e'
_computing_publication_material  SHELXTL

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0490P)²+0.5199P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2941
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0843
_refine_ls_wR_factor_gt          0.0791
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3390(3) 0.50967(16) 0.7082(2) 0.0309(6) Uani 1 1 d . . .
C2 C 0.3237(3) 0.47466(17) 0.8234(2) 0.0317(6) Uani 1 1 d . . .
C3 C 0.2300(5) 0.51276(19) 0.8934(3) 0.0469(8) Uani 1 1 d . . .
H3 H 0.1781 0.5604 0.8695 0.056 Uiso 1 1 calc R . .
C4 C 0.2138(5) 0.4799(2) 0.9986(3) 0.0584(10) Uani 1 1 d . . .
H4 H 0.1535 0.5065 1.0460 0.070 Uiso 1 1 calc R . .
C5 C 0.2851(5) 0.4086(2) 1.0341(3) 0.0508(9) Uani 1 1 d . . .
H5 H 0.2730 0.3871 1.1050 0.061 Uiso 1 1 calc R . .
C6 C 0.3746(4) 0.3692(2) 0.9642(3) 0.0516(9) Uani 1 1 d . . .
H6 H 0.4208 0.3202 0.9867 0.062 Uiso 1 1 calc R . .
C7 C 0.3959(4) 0.40263(19) 0.8601(3) 0.0417(8) Uani 1 1 d . . .
H7 H 0.4594 0.3764 0.8143 0.050 Uiso 1 1 calc R . .
C8 C 0.2172(4) 0.62167(16) 0.2884(2) 0.0330(7) Uani 1 1 d . . .
H8A H 0.3339 0.6354 0.2959 0.040 Uiso 1 1 calc R . .
H8B H 0.1617 0.6315 0.2087 0.040 Uiso 1 1 calc R . .
C9 C 0.2013(4) 0.53563(17) 0.3177(2) 0.0326(6) Uani 1 1 d . . .
H9A H 0.0850 0.5201 0.2998 0.039 Uiso 1 1 calc R . .
H9B H 0.2615 0.5036 0.2711 0.039 Uiso 1 1 calc R . .
C10 C 0.2201(4) 0.74997(17) 0.3897(2) 0.0367(7) Uani 1 1 d . . .
H10A H 0.1769 0.7847 0.3250 0.044 Uiso 1 1 calc R . .
H10B H 0.3394 0.7450 0.3951 0.044 Uiso 1 1 calc R . .
C11 C 0.1850(4) 0.78467(17) 0.5012(3) 0.0402(7) Uani 1 1 d . . .
H11A H 0.2596 0.8287 0.5253 0.048 Uiso 1 1 calc R . .
H11B H 0.0716 0.8043 0.4881 0.048 Uiso 1 1 calc R . .
C12 C -0.0450(4) 0.67694(19) 0.3281(3) 0.0411(7) Uani 1 1 d . . .
H12A H -0.0804 0.6375 0.2683 0.049 Uiso 1 1 calc R . .
H12B H -0.0718 0.7284 0.2932 0.049 Uiso 1 1 calc R . .
C13 C -0.1406(4) 0.6652(2) 0.4253(3) 0.0461(8) Uani 1 1 d . . .
H13A H -0.1246 0.7099 0.4780 0.055 Uiso 1 1 calc R . .
H13B H -0.2587 0.6595 0.3938 0.055 Uiso 1 1 calc R . .
N1 N 0.1404(3) 0.67106(13) 0.36927(19) 0.0282(5) Uani 1 1 d . . .
N2 N 0.5994(4) 0.67404(15) 0.6501(2) 0.0425(6) Uani 1 1 d . . .
O1 O 0.2493(3) 0.56894(12) 0.67531(16) 0.0396(5) Uani 1 1 d . . .
O2 O 0.4387(2) 0.47742(12) 0.65330(17) 0.0367(5) Uani 1 1 d . . .
O3 O 0.2076(3) 0.72582(12) 0.59171(18) 0.0387(5) Uani 1 1 d . . .
O4 O 0.2674(2) 0.52301(11) 0.43890(15) 0.0286(4) Uani 1 1 d . . .
O5 O -0.0761(3) 0.59568(16) 0.4838(3) 0.0560(7) Uani 1 1 d . . .
O6 O 0.5272(3) 0.64815(14) 0.55247(18) 0.0456(5) Uani 1 1 d . . .
O7 O 0.5199(3) 0.71906(15) 0.7066(2) 0.0575(7) Uani 1 1 d . . .
O8 O 0.7450(3) 0.65640(15) 0.6913(2) 0.0596(7) Uani 1 1 d . . .
Cu1 Cu 0.19889(4) 0.613362(19) 0.52255(3) 0.03014(13) Uani 1 1 d . . .
Cu2 Cu 0.5000 0.5000 0.5000 0.02917(15) Uani 1 2 d S . .
H3O3 H 0.300(5) 0.724(2) 0.621(3) 0.061(13) Uiso 1 1 d . . .
H5O5 H -0.139(5) 0.580(3) 0.514(4) 0.072(15) Uiso 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.258(3) . ?
C1 O1 1.260(3) . ?
C1 C2 1.501(4) . ?
C2 C3 1.386(4) . ?
C2 C7 1.388(4) . ?
C3 C4 1.382(5) . ?
C4 C5 1.370(5) . ?
C5 C6 1.374(5) . ?
C6 C7 1.385(4) . ?
C8 N1 1.492(3) . ?
C8 C9 1.509(4) . ?
C9 O4 1.433(3) . ?
C10 N1 1.487(4) . ?
C10 C11 1.510(4) . ?
C11 O3 1.441(4) . ?
C12 N1 1.503(4) . ?
C12 C13 1.515(4) . ?
C13 O5 1.413(4) . ?
N1 Cu1 2.018(2) . ?
N2 O8 1.232(3) . ?
N2 O6 1.259(3) . ?
N2 O7 1.269(3) . ?
O1 Cu1 1.9099(19) . ?
O2 Cu2 1.9933(19) . ?
O3 Cu1 2.067(2) . ?
O4 Cu2 1.9380(18) . ?
O4 Cu1 1.9582(19) . ?
O5 Cu1 2.228(3) . ?
Cu2 O4 1.9380(18) 3_666 ?
Cu2 O2 1.9933(19) 3_666 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 126.0(3) . . ?
O2 C1 C2 117.6(2) . . ?
O1 C1 C2 116.3(3) . . ?
C3 C2 C7 118.6(3) . . ?
C3 C2 C1 120.0(3) . . ?
C7 C2 C1 121.4(3) . . ?
C4 C3 C2 120.0(3) . . ?
C5 C4 C3 121.1(3) . . ?
C4 C5 C6 119.5(3) . . ?
C5 C6 C7 120.0(3) . . ?
C6 C7 C2 120.9(3) . . ?
N1 C8 C9 109.4(2) . . ?
O4 C9 C8 109.6(2) . . ?
N1 C10 C11 109.7(2) . . ?
O3 C11 C10 110.3(2) . . ?
N1 C12 C13 112.8(2) . . ?
O5 C13 C12 106.0(3) . . ?
C10 N1 C8 112.4(2) . . ?
C10 N1 C12 112.1(2) . . ?
C8 N1 C12 111.0(2) . . ?
C10 N1 Cu1 105.81(16) . . ?
C8 N1 Cu1 103.66(16) . . ?
C12 N1 Cu1 111.51(17) . . ?
O8 N2 O6 121.1(3) . . ?
O8 N2 O7 119.8(3) . . ?
O6 N2 O7 119.1(3) . . ?
C1 O1 Cu1 127.36(19) . . ?
C1 O2 Cu2 132.81(18) . . ?
C11 O3 Cu1 111.13(16) . . ?
C9 O4 Cu2 123.33(17) . . ?
C9 O4 Cu1 106.79(16) . . ?
Cu2 O4 Cu1 109.26(9) . . ?
C13 O5 Cu1 104.69(19) . . ?
O1 Cu1 O4 97.45(8) . . ?
O1 Cu1 N1 173.92(9) . . ?
O4 Cu1 N1 88.59(8) . . ?
O1 Cu1 O3 90.69(9) . . ?
O4 Cu1 O3 157.81(9) . . ?
N1 Cu1 O3 83.43(9) . . ?
O1 Cu1 O5 99.33(10) . . ?
O4 Cu1 O5 99.80(9) . . ?
N1 Cu1 O5 80.19(9) . . ?
O3 Cu1 O5 99.19(10) . . ?
O4 Cu2 O4 180.0 . 3_666 ?
O4 Cu2 O2 91.80(8) . 3_666 ?
O4 Cu2 O2 88.20(8) 3_666 3_666 ?
O4 Cu2 O2 88.20(8) . . ?
O4 Cu2 O2 91.80(8) 3_666 . ?
O2 Cu2 O2 180.000(1) 3_666 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C3 172.9(3) . . . . ?
O1 C1 C2 C3 -7.4(4) . . . . ?
O2 C1 C2 C7 -9.9(4) . . . . ?
O1 C1 C2 C7 169.8(3) . . . . ?
C7 C2 C3 C4 1.7(5) . . . . ?
C1 C2 C3 C4 179.0(3) . . . . ?
C2 C3 C4 C5 -1.9(6) . . . . ?
C3 C4 C5 C6 0.2(6) . . . . ?
C4 C5 C6 C7 1.7(6) . . . . ?
C5 C6 C7 C2 -1.9(5) . . . . ?
C3 C2 C7 C6 0.2(5) . . . . ?
C1 C2 C7 C6 -177.1(3) . . . . ?
N1 C8 C9 O4 -53.2(3) . . . . ?
N1 C10 C11 O3 44.2(3) . . . . ?
N1 C12 C13 O5 -49.5(4) . . . . ?
C11 C10 N1 C8 -159.3(2) . . . . ?
C11 C10 N1 C12 74.9(3) . . . . ?
C11 C10 N1 Cu1 -46.8(3) . . . . ?
C9 C8 N1 C10 150.7(2) . . . . ?
C9 C8 N1 C12 -82.9(3) . . . . ?
C9 C8 N1 Cu1 36.9(2) . . . . ?
C13 C12 N1 C10 -98.5(3) . . . . ?
C13 C12 N1 C8 134.9(3) . . . . ?
C13 C12 N1 Cu1 19.9(3) . . . . ?
O2 C1 O1 Cu1 14.9(4) . . . . ?
C2 C1 O1 Cu1 -164.81(19) . . . . ?
O1 C1 O2 Cu2 -0.6(4) . . . . ?
C2 C1 O2 Cu2 179.08(18) . . . . ?
C10 C11 O3 Cu1 -19.3(3) . . . . ?
C8 C9 O4 Cu2 -87.9(3) . . . . ?
C8 C9 O4 Cu1 39.8(3) . . . . ?
C12 C13 O5 Cu1 51.1(3) . . . . ?
C1 O1 Cu1 O4 16.2(2) . . . . ?
C1 O1 Cu1 N1 -157.5(8) . . . . ?
C1 O1 Cu1 O3 -143.1(2) . . . . ?
C1 O1 Cu1 O5 117.5(2) . . . . ?
C9 O4 Cu1 O1 165.65(17) . . . . ?
Cu2 O4 Cu1 O1 -58.84(10) . . . . ?
C9 O4 Cu1 N1 -15.01(17) . . . . ?
Cu2 O4 Cu1 N1 120.50(10) . . . . ?
C9 O4 Cu1 O3 -83.7(3) . . . . ?
Cu2 O4 Cu1 O3 51.8(2) . . . . ?
C9 O4 Cu1 O5 64.78(17) . . . . ?
Cu2 O4 Cu1 O5 -159.70(10) . . . . ?
C10 N1 Cu1 O1 42.8(9) . . . . ?
C8 N1 Cu1 O1 161.2(8) . . . . ?
C12 N1 Cu1 O1 -79.3(9) . . . . ?
C10 N1 Cu1 O4 -130.98(18) . . . . ?
C8 N1 Cu1 O4 -12.56(16) . . . . ?
C12 N1 Cu1 O4 106.91(19) . . . . ?
C10 N1 Cu1 O3 28.28(18) . . . . ?
C8 N1 Cu1 O3 146.70(18) . . . . ?
C12 N1 Cu1 O3 -93.83(19) . . . . ?
C10 N1 Cu1 O5 128.83(19) . . . . ?
C8 N1 Cu1 O5 -112.75(18) . . . . ?
C12 N1 Cu1 O5 6.72(19) . . . . ?
C11 O3 Cu1 O1 176.2(2) . . . . ?
C11 O3 Cu1 O4 64.4(3) . . . . ?
C11 O3 Cu1 N1 -5.3(2) . . . . ?
C11 O3 Cu1 O5 -84.2(2) . . . . ?
C13 O5 Cu1 O1 140.3(2) . . . . ?
C13 O5 Cu1 O4 -120.4(2) . . . . ?
C13 O5 Cu1 N1 -33.6(2) . . . . ?
C13 O5 Cu1 O3 48.0(2) . . . . ?
C9 O4 Cu2 O4 0(100) . . . 3_666 ?
Cu1 O4 Cu2 O4 0(100) . . . 3_666 ?
C9 O4 Cu2 O2 9.0(2) . . . 3_666 ?
Cu1 O4 Cu2 O2 -117.61(10) . . . 3_666 ?
C9 O4 Cu2 O2 -171.0(2) . . . . ?
Cu1 O4 Cu2 O2 62.39(10) . . . . ?
C1 O2 Cu2 O4 -39.5(3) . . . . ?
C1 O2 Cu2 O4 140.5(3) . . . 3_666 ?
C1 O2 Cu2 O2 21(100) . . . 3_666 ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.074

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1474750'
_audit_update_record             
;
2016-09-23 deposited with the CCDC.
2016-10-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C27 H31 N O10 Zn2'
_chemical_formula_sum            'C27 H31 N O10 Zn2'
_chemical_melting_point          ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless

_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         660.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.49(4)
_cell_length_b                   11.44(3)
_cell_length_c                   18.17(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.49(5)
_cell_angle_gamma                90
_cell_volume                     2839(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      25.50
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    1.746
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.6406
_exptl_absorpt_correction_T_max  0.7675
_exptl_absorpt_process_details   Sadabs

_exptl_special_details           
;
 ?
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEX'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            34548
_diffrn_reflns_av_R_equivalents  0.0791
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4985
_reflns_number_gt                3220
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND 2.1e'
_computing_publication_material  SHELXTL

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0329P)²+0.9727P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4985
_refine_ls_number_parameters     377
_refine_ls_number_restraints     133
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.0898
_refine_ls_wR_factor_gt          0.0785
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5636(3) 0.3815(3) -0.1858(2) 0.0468(10) Uani 1 1 d U . .
C2 C 0.5593(3) 0.4637(3) -0.2517(2) 0.0442(9) Uani 1 1 d U . .
C3 C 0.4856(3) 0.4543(4) -0.3229(2) 0.0665(13) Uani 1 1 d U . .
H3 H 0.4376 0.3972 -0.3305 0.080 Uiso 1 1 calc R . .
C4 C 0.4831(3) 0.5300(5) -0.3829(3) 0.0896(17) Uani 1 1 d U . .
H4 H 0.4345 0.5217 -0.4313 0.108 Uiso 1 1 calc R . .
C5 C 0.5512(4) 0.6169(5) -0.3719(3) 0.0925(17) Uani 1 1 d U . .
H5 H 0.5478 0.6686 -0.4122 0.111 Uiso 1 1 calc R . .
C6 C 0.6239(4) 0.6273(4) -0.3018(3) 0.0812(15) Uani 1 1 d U . .
H6 H 0.6706 0.6860 -0.2942 0.097 Uiso 1 1 calc R . .
C7 C 0.6282(3) 0.5508(4) -0.2422(2) 0.0600(11) Uani 1 1 d U . .
H7 H 0.6786 0.5580 -0.1947 0.072 Uiso 1 1 calc R . .
C8 C 0.8521(3) 0.3487(3) 0.0897(2) 0.0498(10) Uani 1 1 d U . .
C9 C 0.9442(3) 0.4158(3) 0.1282(2) 0.0434(9) Uani 1 1 d U . .
C10 C 1.0011(3) 0.3912(4) 0.2043(2) 0.0539(11) Uani 1 1 d U . .
H10 H 0.9804 0.3352 0.2325 0.065 Uiso 1 1 calc R . .
C11 C 1.0880(3) 0.4487(4) 0.2385(2) 0.0627(12) Uani 1 1 d U . .
H11 H 1.1265 0.4304 0.2894 0.075 Uiso 1 1 calc R . .
C12 C 1.1181(3) 0.5323(4) 0.1984(2) 0.0638(12) Uani 1 1 d U . .
H12 H 1.1768 0.5716 0.2222 0.077 Uiso 1 1 calc R . .
C13 C 1.0626(3) 0.5591(4) 0.1231(3) 0.0656(12) Uani 1 1 d U . .
H13 H 1.0836 0.6159 0.0957 0.079 Uiso 1 1 calc R . .
C14 C 0.9752(3) 0.5014(4) 0.0880(2) 0.0572(11) Uani 1 1 d U . .
H14 H 0.9370 0.5201 0.0372 0.069 Uiso 1 1 calc R . .
C15 C 0.7317(3) 0.0333(4) -0.0080(2) 0.0470(10) Uani 1 1 d U . .
C16 C 0.7516(3) -0.0872(4) -0.0311(2) 0.0466(10) Uani 1 1 d U . .
C17 C 0.7368(3) -0.1821(4) 0.0096(2) 0.0645(12) Uani 1 1 d U . .
H17 H 0.7120 -0.1715 0.0502 0.077 Uiso 1 1 calc R . .
C18 C 0.7584(4) -0.2932(4) -0.0092(3) 0.0842(16) Uani 1 1 d U . .
H18 H 0.7473 -0.3571 0.0184 0.101 Uiso 1 1 calc R . .
C19 C 0.7961(4) -0.3101(5) -0.0680(3) 0.0943(19) Uani 1 1 d U . .
H19 H 0.8123 -0.3850 -0.0795 0.113 Uiso 1 1 calc R . .
C20 C 0.8097(4) -0.2171(5) -0.1096(3) 0.0877(17) Uani 1 1 d U . .
H20 H 0.8342 -0.2287 -0.1502 0.105 Uiso 1 1 calc R . .
C21 C 0.7874(3) -0.1046(4) -0.0920(2) 0.0637(12) Uani 1 1 d U . .
H21 H 0.7966 -0.0414 -0.1209 0.076 Uiso 1 1 calc R . .
C22 C 0.7072(3) 0.3065(4) 0.2612(2) 0.0659(12) Uani 1 1 d U . .
H22A H 0.6765 0.3426 0.2955 0.079 Uiso 1 1 calc R . .
H22B H 0.7587 0.3580 0.2577 0.079 Uiso 1 1 calc R . .
C23 C 0.7502(3) 0.1903(4) 0.2943(2) 0.0623(12) Uani 1 1 d U . .
H23A H 0.8031 0.2025 0.3431 0.075 Uiso 1 1 calc R . .
H23B H 0.7004 0.1431 0.3049 0.075 Uiso 1 1 calc R . .
C24 C 0.5404(3) 0.2398(4) 0.1868(3) 0.0765(13) Uani 1 1 d U . .
H24A H 0.5492 0.2216 0.2409 0.092 Uiso 1 1 calc R . .
H24B H 0.4892 0.2983 0.1695 0.092 Uiso 1 1 calc R . .
C25 C 0.5087(3) 0.1337(5) 0.1395(3) 0.0849(16) Uani 1 1 d U . .
H25A H 0.4661 0.0886 0.1601 0.102 Uiso 1 1 calc R . .
H25B H 0.4714 0.1558 0.0864 0.102 Uiso 1 1 calc R . .
C26 C 0.6164(3) 0.3961(4) 0.1327(2) 0.0691(13) Uani 1 1 d U . .
H26A H 0.6787 0.4339 0.1395 0.083 Uiso 1 1 calc R . .
H26B H 0.5758 0.4505 0.1492 0.083 Uiso 1 1 calc R . .
C27 C 0.5670(3) 0.3664(4) 0.0474(2) 0.0658(12) Uani 1 1 d U . .
H27A H 0.4980 0.3518 0.0377 0.079 Uiso 1 1 calc R . .
H27B H 0.5723 0.4325 0.0156 0.079 Uiso 1 1 calc R . .
N1 N 0.6331(2) 0.2898(3) 0.18210(19) 0.0553(9) Uani 1 1 d U . .
O1 O 0.64829(19) 0.3666(3) -0.13612(14) 0.0671(8) Uani 1 1 d U . .
O2 O 0.48748(19) 0.3336(2) -0.18405(14) 0.0529(7) Uani 1 1 d U . .
O3 O 0.82289(17) 0.2781(2) 0.12996(15) 0.0541(7) Uani 1 1 d U . .
O4 O 0.80877(18) 0.3679(2) 0.01716(14) 0.0652(8) Uani 1 1 d U . .
O5 O 0.72812(19) 0.0440(2) 0.05981(15) 0.0543(7) Uani 1 1 d U . .
O6 O 0.72230(19) 0.1161(2) -0.05640(15) 0.0589(7) Uani 1 1 d U . .
O7 O 0.7867(2) 0.1298(3) 0.24035(16) 0.0498(8) Uani 1 1 d U . .
O8 O 0.60992(17) 0.2663(2) 0.02535(14) 0.0465(6) Uani 1 1 d U . .
O9 O 0.5862(2) 0.0653(3) 0.1390(2) 0.0719(9) Uani 1 1 d U . .
O10 O 0.5358(3) 0.8503(3) 0.0893(3) 0.0712(10) Uani 1 1 d . . .
Zn1 Zn 0.69848(3) 0.17365(4) 0.12132(2) 0.04227(15) Uani 1 1 d U . .
Zn2 Zn 0.69131(3) 0.27872(4) -0.04025(3) 0.05122(16) Uani 1 1 d U . .
H7A H 0.838(3) 0.143(4) 0.254(3) 0.067(18) Uiso 1 1 d . . .
H9 H 0.574(5) 0.000(6) 0.117(4) 0.17(3) Uiso 1 1 d . . .
H10A H 0.531(3) 0.809(4) 0.121(3) 0.071(19) Uiso 1 1 d . . .
H10B H 0.496(4) 0.830(5) 0.049(3) 0.13(3) Uiso 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.242(5) . ?
C1 O1 1.269(5) . ?
C1 C2 1.508(6) . ?
C2 C3 1.379(6) . ?
C2 C7 1.381(6) . ?
C3 C4 1.383(6) . ?
C4 C5 1.368(7) . ?
C5 C6 1.361(7) . ?
C6 C7 1.378(6) . ?
C8 O3 1.255(5) . ?
C8 O4 1.275(5) . ?
C8 C9 1.495(6) . ?
C9 C14 1.382(6) . ?
C9 C10 1.383(6) . ?
C10 C11 1.372(6) . ?
C11 C12 1.360(6) . ?
C12 C13 1.371(6) . ?
C13 C14 1.381(6) . ?
C15 O5 1.256(5) . ?
C15 O6 1.269(5) . ?
C15 C16 1.497(6) . ?
C16 C17 1.371(6) . ?
C16 C21 1.384(6) . ?
C17 C18 1.379(7) . ?
C18 C19 1.367(8) . ?
C19 C20 1.357(8) . ?
C20 C21 1.389(7) . ?
C22 N1 1.492(6) . ?
C22 C23 1.506(6) . ?
C23 O7 1.437(5) . ?
C24 C25 1.470(7) . ?
C24 N1 1.489(6) . ?
C25 O9 1.371(6) . ?
C26 N1 1.483(6) . ?
C26 C27 1.514(7) . ?
C27 O8 1.423(5) . ?
N1 Zn1 2.140(5) . ?
O1 Zn2 1.926(5) . ?
O3 Zn1 2.124(5) . ?
O4 Zn2 1.960(4) . ?
O5 Zn1 1.989(5) . ?
O6 Zn2 1.959(6) . ?
O7 Zn1 2.172(6) . ?
O8 Zn2 1.942(5) . ?
O8 Zn1 2.078(4) . ?
O9 Zn1 2.153(5) . ?
Zn1 Zn2 3.142(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 125.4(4) . . ?
O2 C1 C2 119.6(3) . . ?
O1 C1 C2 115.0(4) . . ?
C3 C2 C7 118.3(4) . . ?
C3 C2 C1 120.7(4) . . ?
C7 C2 C1 121.0(4) . . ?
C2 C3 C4 119.9(4) . . ?
C5 C4 C3 120.8(4) . . ?
C6 C5 C4 119.7(5) . . ?
C5 C6 C7 119.8(5) . . ?
C6 C7 C2 121.3(4) . . ?
O3 C8 O4 124.6(4) . . ?
O3 C8 C9 118.6(4) . . ?
O4 C8 C9 116.8(4) . . ?
C14 C9 C10 118.8(4) . . ?
C14 C9 C8 120.8(4) . . ?
C10 C9 C8 120.4(4) . . ?
C11 C10 C9 120.5(4) . . ?
C12 C11 C10 120.3(4) . . ?
C11 C12 C13 120.4(4) . . ?
C12 C13 C14 119.7(4) . . ?
C13 C14 C9 120.4(4) . . ?
O5 C15 O6 125.3(4) . . ?
O5 C15 C16 116.1(4) . . ?
O6 C15 C16 118.6(4) . . ?
C17 C16 C21 119.0(4) . . ?
C17 C16 C15 119.8(4) . . ?
C21 C16 C15 121.1(4) . . ?
C16 C17 C18 120.4(5) . . ?
C19 C18 C17 120.5(5) . . ?
C20 C19 C18 119.7(5) . . ?
C19 C20 C21 120.6(5) . . ?
C16 C21 C20 119.7(5) . . ?
N1 C22 C23 109.9(3) . . ?
O7 C23 C22 110.5(4) . . ?
C25 C24 N1 113.3(4) . . ?
O9 C25 C24 112.3(4) . . ?
N1 C26 C27 111.2(4) . . ?
O8 C27 C26 111.5(3) . . ?
C26 N1 C24 112.4(3) . . ?
C26 N1 C22 113.4(3) . . ?
C24 N1 C22 111.5(4) . . ?
C26 N1 Zn1 102.0(3) . . ?
C24 N1 Zn1 110.8(3) . . ?
C22 N1 Zn1 106.1(3) . . ?
C1 O1 Zn2 131.2(3) . . ?
C8 O3 Zn1 139.6(2) . . ?
C8 O4 Zn2 120.1(3) . . ?
C15 O5 Zn1 135.3(3) . . ?
C15 O6 Zn2 125.6(3) . . ?
C23 O7 Zn1 109.8(3) . . ?
C27 O8 Zn2 121.7(3) . . ?
C27 O8 Zn1 112.3(3) . . ?
Zn2 O8 Zn1 102.8(2) . . ?
C25 O9 Zn1 109.5(3) . . ?
O5 Zn1 O8 95.6(2) . . ?
O5 Zn1 O3 97.12(19) . . ?
O8 Zn1 O3 92.66(19) . . ?
O5 Zn1 N1 165.68(12) . . ?
O8 Zn1 N1 82.0(2) . . ?
O3 Zn1 N1 97.1(2) . . ?
O5 Zn1 O9 88.3(2) . . ?
O8 Zn1 O9 97.6(2) . . ?
O3 Zn1 O9 167.86(12) . . ?
N1 Zn1 O9 78.1(2) . . ?
O5 Zn1 O7 102.8(2) . . ?
O8 Zn1 O7 161.24(11) . . ?
O3 Zn1 O7 81.55(16) . . ?
N1 Zn1 O7 81.1(2) . . ?
O9 Zn1 O7 86.67(19) . . ?
O5 Zn1 Zn2 72.9(2) . . ?
O8 Zn1 Zn2 37.06(13) . . ?
O3 Zn1 Zn2 67.45(10) . . ?
N1 Zn1 Zn2 111.24(19) . . ?
O9 Zn1 Zn2 124.65(11) . . ?
O7 Zn1 Zn2 147.52(15) . . ?
O1 Zn2 O8 120.93(19) . . ?
O1 Zn2 O6 112.41(19) . . ?
O8 Zn2 O6 103.83(13) . . ?
O1 Zn2 O4 99.86(18) . . ?
O8 Zn2 O4 108.0(2) . . ?
O6 Zn2 O4 111.87(19) . . ?
O1 Zn2 Zn1 160.86(11) . . ?
O8 Zn2 Zn1 40.17(12) . . ?
O6 Zn2 Zn1 80.73(15) . . ?
O4 Zn2 Zn1 87.12(16) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.068

